Rock musician and visual artist Don Van Vliet, best known by his stage name Captain Beefheart, died Friday at 69, Entertainment Weekly reported.

Van Vliet, who forged a close creative partnership with high school friend Frank Zappa, died of complications from multiple sclerosis at a hospital in northern California, EW said.

In 1969, Zappa produced Van Vliet’s “Trout Mask Replica,” which came to be regarded as a landmark avant-garde rock album.

Born January 15, 1941 in Glendale, California, he began performing as Captain Beefheart in 1964 and joined The Magic Band in 1965, recording 12 studio albums with them.

Known for his powerful singing voice and avant-garde rock style, Van Vliet retired his Beefheart persona in 1982 to pursue a career in art. The Michael Werner Gallery in New York displayed his work for decades.

Earlier this month, it said, one of Van Vliet’s paintings was reportedly being offered at an asking price of $40,000.